Propargyl alcohol → 3-(3,4-Dichlorophenyl)prop-2-yn-1-ol

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Propargyl alcohol	HCID 7859	—
Edukt	Triphenylphosphine	HCID 11776	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Benzene, 1,2-dichloro-4-iodo-	HCID 88591	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Lösungsmittel	Sodium chloride; water	HCID 57417360	—
Produkt	3-(3,4-Dichlorophenyl)prop-2-yn-1-ol	HCID 23006381	—

Reaktionsschritte

A mixture of 3,4-dichloroiodobenzene (5.00 g), copper(I) iodide (69.8 mg), triphenylphosphine (240 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (378 mg), propargyl alcohol (1.19 ml), diisopropylethylamine (12.8 ml) and tetrahydrofuran (80 ml) was stirred at room temperature for 5 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-80:20) to give the object product (3.21 g) as a pale-brown solid.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08129361B2
Quelldatensatz	uspto-grants-2012_03
ORD ID	ord-ce678e3eea8d47b9ad8342668226e423
Quellennotiz	uspto-grants-2012_03